6-Octadecenoic acid (BioDeep_00000228143)

   

human metabolite natural product


代谢物信息卡片


petroselinic acid, sodium salt, (Z)-isomer

化学式: C18H34O2 (282.2559)
中文名称: 石油硬脂酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCCCCC=CCCCCC(=O)O
InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)/b13-12+

描述信息

Isolated from volatiles of Coriandrum sativum (coriander), Anethum sowa (Indian dill), Cuminum cyminum (cumin), Daucus carota (carrot), Nigella sativa (black cumin), Apium graveolens (celery), Pimpinella anisum (anise) and Petroselinum sativum (parsley) [CCD]. 6-Octadecenoic acid is found in dill.
Minor constituent of plant oils. Constituent of milk fat and from porcine parasites Oesophagostomum dentatum and Oesophagostomum quadrispinulatum [CCD]. Petroselaidic acid is found in fats and oils.

同义名列表

24 个代谢物同义名

petroselinic acid, sodium salt, (Z)-isomer; trans-Delta(6)-Octadecenoic acid; petroselinic acid, (Z)-isomer; petroselinic acid, (E)-isomer; trans-Δ(6)-octadecenoic acid; trans-delta(6)-Octadecenoate; trans-Octadec-6-enoic acid; (6E)-octadec-6-enoic acid; trans-6-octadecenoic acid; trans-Δ(6)-octadecenoate; (6E)-6-Octadecenoic acid; trans-Octadec-6-enoate; Octadec-6t-enoic acid; trans-6-Octadecenoate; 6E-octadecenoic acid; Octadec-6t-ensaeure; 6-octadecenoic acid; Petroselaidic acid; petroselenic acid; Petroselinic acid; Octadec-6t-enoate; 6E-Octadecenoate; 6-Octadecenoate; Petroselaidate



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

15 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ACE, CAT, DHFR, FGFR4, NT5C2, PCK1, PLA2G12A, PTGS1, PTGS2
Peripheral membrane protein 3 ACHE, PTGS1, PTGS2
Endoplasmic reticulum membrane 3 PLD2, PTGS1, PTGS2
Nucleus 3 ACHE, MN1, PPARGC1A
cytosol 6 CAT, DHFR, LIPE, NT5C2, PCK1, PPARGC1A
nucleoplasm 3 ATP2B1, OLR1, PPARGC1A
Cell membrane 7 ACE, ACHE, ATP2B1, FGFR4, LIPE, OLR1, PLD2
Lipid-anchor 2 OLR1, PLD2
Multi-pass membrane protein 1 ATP2B1
Synapse 2 ACHE, ATP2B1
cell surface 1 ACHE
glutamatergic synapse 1 ATP2B1
Golgi apparatus 3 ACHE, FGFR4, PTGS1
Golgi membrane 1 INS
neuromuscular junction 1 ACHE
presynaptic membrane 1 ATP2B1
Cytoplasm, cytosol 3 LIPE, NT5C2, PCK1
Lysosome 1 ACE
Presynapse 1 PLD2
endosome 2 ACE, FGFR4
plasma membrane 6 ACE, ACHE, ATP2B1, FGFR4, OLR1, PLD2
synaptic vesicle membrane 1 ATP2B1
Membrane 7 ACE, ACHE, ATP2B1, CAT, FGFR4, LIPE, OLR1
basolateral plasma membrane 1 ATP2B1
caveola 2 LIPE, PTGS2
extracellular exosome 5 ACE, ATP2B1, CAT, PCK1, PTGS1
endoplasmic reticulum 3 FGFR4, PCK1, PTGS2
extracellular space 4 ACE, ACHE, IFNA1, INS
perinuclear region of cytoplasm 1 ACHE
mitochondrion 3 CAT, DHFR, PCK2
protein-containing complex 2 CAT, PTGS2
intracellular membrane-bounded organelle 5 ATP2B1, CAT, OLR1, PLD2, PTGS1
Microsome membrane 2 PTGS1, PTGS2
Single-pass type I membrane protein 2 ACE, FGFR4
Secreted 6 ACE, ACHE, IFNA1, INS, OLR1, PLA2G12A
extracellular region 7 ACE, ACHE, CAT, FGFR4, INS, OLR1, PLA2G12A
mitochondrial matrix 2 CAT, PCK2
Extracellular side 1 ACHE
photoreceptor outer segment 1 PTGS1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 1 ACE
Single-pass type II membrane protein 1 OLR1
Membrane raft 1 OLR1
focal adhesion 1 CAT
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 PPARGC1A
PML body 1 PPARGC1A
lateral plasma membrane 1 ATP2B1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 2 FGFR4, OLR1
neuron projection 2 PTGS1, PTGS2
chromatin 1 PPARGC1A
cell projection 1 ATP2B1
brush border membrane 1 ACE
sperm midpiece 1 ACE
Basolateral cell membrane 1 ATP2B1
Lipid-anchor, GPI-anchor 1 ACHE
Endomembrane system 1 PTGS1
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
specific granule membrane 1 OLR1
tertiary granule membrane 1 OLR1
Presynaptic cell membrane 1 ATP2B1
side of membrane 1 ACHE
basal plasma membrane 1 ACE
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, PTGS2
transport vesicle 2 FGFR4, INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 ATP2B1
[Isoform 1]: Nucleus 1 PPARGC1A
synaptic cleft 1 ACHE
catalase complex 1 CAT
photoreceptor ribbon synapse 1 ATP2B1
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
[Isoform H]: Cell membrane 1 ACHE
[Isoform B4]: Nucleus 1 PPARGC1A
[Isoform B4-8a]: Cytoplasm 1 PPARGC1A
[Isoform B5]: Nucleus 1 PPARGC1A
[Isoform 9]: Nucleus 1 PPARGC1A


文献列表

  • Ahmed Hajib, Said El Harkaoui, Hasnae Choukri, Aya Khouchlaa, Sarra Aourabi, Naoual El Menyiy, Abdelhakim Bouyahya, Bertrand Matthaeus. Apiaceae Family an Important Source of Petroselinic Fatty Acid: Abundance, Biosynthesis, Chemistry, and Biological Proprieties. Biomolecules. 2023 11; 13(11):. doi: 10.3390/biom13111675. [PMID: 38002357]
  • Zheng Yang, Changsheng Li, Qingli Jia, Cuizhu Zhao, David C Taylor, Dawei Li, Meng Zhang. Transcriptome Analysis Reveals Candidate Genes for Petroselinic Acid Biosynthesis in Fruits of Coriandrum sativum L. Journal of agricultural and food chemistry. 2020 May; 68(19):5507-5520. doi: 10.1021/acs.jafc.0c01487. [PMID: 32320606]
  • Juergen K R Wanner, Do N Dai, Le T Huong, Nguyen V Hung, Erich Schmidt, Leopold Jirovetz. Fatty Acid Methyl Ester Composition of Some Turkish Apiaceae Seed Oils: New Sources for Petroselinic Acid. Natural product communications. 2016 Nov; 11(11):1697-1700. doi: ". [PMID: 30475510]
  • Evelien Uitterhaegen, Klicia A Sampaio, Elisabeth I P Delbeke, Wim De Greyt, Muriel Cerny, Philippe Evon, Othmane Merah, Thierry Talou, Christian V Stevens. Characterization of French Coriander Oil as Source of Petroselinic Acid. Molecules (Basel, Switzerland). 2016 Sep; 21(9):. doi: 10.3390/molecules21091202. [PMID: 27617992]
  • Najla Gooda Sahib, Farooq Anwar, Anwarul-Hassan Gilani, Azizah Abdul Hamid, Nazamid Saari, Khalid M Alkharfy. Coriander (Coriandrum sativum L.): a potential source of high-value components for functional foods and nutraceuticals--a review. Phytotherapy research : PTR. 2013 Oct; 27(10):1439-56. doi: 10.1002/ptr.4897. [PMID: 23281145]
  • Antonio Ruiz-Vela, Cristóbal Aguilar-Gallardo, Ana M Martínez-Arroyo, Mario Soriano-Navarro, Verónica Ruiz, Carlos Simón. Specific unsaturated fatty acids enforce the transdifferentiation of human cancer cells toward adipocyte-like cells. Stem cell reviews and reports. 2011 Nov; 7(4):898-909. doi: 10.1007/s12015-011-9253-7. [PMID: 21499706]
  • Iness Bettaieb, Soumaya Bourgou, Jezia Sriti, Kamel Msaada, Ferid Limam, Brahim Marzouk. Essential oils and fatty acids composition of Tunisian and Indian cumin (Cuminum cyminum L.) seeds: a comparative study. Journal of the science of food and agriculture. 2011 Aug; 91(11):2100-7. doi: 10.1002/jsfa.4513. [PMID: 21681765]
  • Bochra Laribi, Karima Kouki, Abdelaziz Mougou, Brahim Marzouk. Fatty acid and essential oil composition of three Tunisian caraway (Carum carvi L.) seed ecotypes. Journal of the science of food and agriculture. 2010 Feb; 90(3):391-6. doi: 10.1002/jsfa.3827. [PMID: 20355058]
  • Xiuying Li, Yanhong Zhu, Tong Wu, Shuzhen Zhang, Peter Christie. Using a novel petroselinic Acid embedded cellulose acetate membrane to mimic plant partitioning and in vivo uptake of polycyclic aromatic hydrocarbons. Environmental science & technology. 2010 Jan; 44(1):297-301. doi: 10.1021/es902283x. [PMID: 19950922]
  • N Tsevegsuren, K Aitzetmuller, K Vosmann. Geranium sanguineum (Geraniaceae) seed oil: a new source of petroselinic and vernolic acid. Lipids. 2004 Jun; 39(6):571-6. doi: 10.1007/s11745-004-1265-8. [PMID: 15554157]
  • Sébastien Guiet, Richard J Robins, Michele Lees, Isabelle Billault. Quantitative 2H NMR analysis of deuterium distribution in petroselinic acid isolated from parsley seed. Phytochemistry. 2003 Sep; 64(1):227-33. doi: 10.1016/s0031-9422(03)00278-4. [PMID: 12946421]
  • Mi Chung Suh, David J Schultz, John B Ohlrogge. What limits production of unusual monoenoic fatty acids in transgenic plants?. Planta. 2002 Aug; 215(4):584-95. doi: 10.1007/s00425-002-0751-3. [PMID: 12172841]
  • Frederic Destaillats, Joseph Arul, James E Simon, Robert L Wolff, Paul Angers. Dibutyrate derivatization of monoacylglycerols for the resolution of regioisomers of oleic, petroselinic, and cis-vaccenic acids. Lipids. 2002 Jan; 37(1):111-6. doi: 10.1007/s11745-002-0870-x. [PMID: 11876258]
  • S Mekhedov, E B Cahoon, J Ohlrogge. An unusual seed-specific 3-ketoacyl-ACP synthase associated with the biosynthesis of petroselinic acid in coriander. Plant molecular biology. 2001 Nov; 47(4):507-18. doi: 10.1023/a:1011832611885. [PMID: 11669576]
  • P Avato, F P Fanizzi, I Rosito. The genus Thapsia as a source of petroselinic acid. Lipids. 2001 Aug; 36(8):845-50. doi: 10.1007/s11745-001-0794-5. [PMID: 11592737]
  • N Weber, S Schönwiese, E Klein, K D Mukherjee. Adipose tissue triacylglycerols of rats are modulated differently by dietary isomeric octadecenoic acids from coriander oil and high oleic sunflower oil. The Journal of nutrition. 1999 Dec; 129(12):2206-11. doi: 10.1093/jn/129.12.2006. [PMID: 10573551]
  • Y Takeuchi, Y Yamaoka, S Fukushima, K Miyawaki, K Taguchi, H Yasukawa, S Kishimoto, M Suzuki. Skin penetration enhancing action of cis-unsaturated fatty acids with omega-9, and omega-12-chain lengths. Biological & pharmaceutical bulletin. 1998 May; 21(5):484-91. doi: 10.1248/bpb.21.484. [PMID: 9635505]
  • K D Richter, K D Mukherjee, N Weber. Fat infiltration in liver of rats induced by different dietary plant oils: high oleic-, medium oleic- and high petroselinic acid-oils. Zeitschrift fur Ernahrungswissenschaft. 1996 Sep; 35(3):241-8. doi: 10.1007/bf01625687. [PMID: 8896286]
  • N Weber, K D Richter, E Schulte, K D Mukherjee. Petroselinic acid from dietary triacylglycerols reduces the concentration of arachidonic acid in tissue lipids of rats. The Journal of nutrition. 1995 Jun; 125(6):1563-8. doi: 10.1093/jn/125.6.1563. [PMID: 7782911]
  • S L Marcus, K S Miyata, R A Rachubinski, J P Capone. Transactivation by PPAR/RXR heterodimers in yeast is potentiated by exogenous fatty acid via a pathway requiring intact peroxisomes. Gene expression. 1995; 4(4-5):227-39. doi: . [PMID: 7787415]
  • E B Cahoon, P Dörmann, J B Ohlrogge. Petroselinic acid biosynthesis and production in transgenic plants. Progress in lipid research. 1994; 33(1-2):155-63. doi: 10.1016/0163-7827(94)90018-3. [PMID: 8190735]
  • E B Cahoon, J Shanklin, J B Ohlrogge. Expression of a coriander desaturase results in petroselinic acid production in transgenic tobacco. Proceedings of the National Academy of Sciences of the United States of America. 1992 Dec; 89(23):11184-8. doi: 10.1073/pnas.89.23.11184. [PMID: 1454797]